Systematic Analysis of Pharmaceutical Preparations of Chondroitin Sulfate Combined with Glucosamine

Abstract

Glycosaminoglycans are carbohydrate-based compounds widely employed as nutraceuticals or prescribed drugs. Oral formulations of chondroitin sulfate combined with glucosamine sulfate have been increasingly used to treat the symptoms of osteoarthritis and osteoarthrosis. The chondroitin sulfate of these combinations can be obtained from shark or bovine cartilages and hence presents differences regarding the proportions of 4- and 6-sulfated N-acetyl β-d-galactosamine units. Herein, we proposed a systematic protocol to assess pharmaceutical batches of this combination drug. Chemical analyses on the amounts of chondroitin sulfate and glucosamine in the batches were in accordance with those declared by the manufacturers. Anion-exchange chromatography has proven more effective than electrophoresis to determine the type of chondroitin sulfate present in the combinations and to detect the presence of keratan sulfate, a common contaminant found in batches prepared with shark chondroitin sulfate. 1D NMR spectra revealed the presence of non-sulfated instead of sulfated glucosamine in the formulations and thus in disagreement with the claims declared on the label. Moreover, 1D and 2D NMR analyses allowed a precise determination on the chemical structures of the chondroitin sulfate present in the formulations. The set of analytical tools suggested here could be useful as guidelines to improve the quality of this medication.

Strategies for optimising musculoskeletal health in the 21st century

“…At relatively high concentrations, glucosamine has been shown to have a protective effect on cartilage and synovial fluid; however many clinical trials have shown that this substance is unable to reach the tissue that it is meant to affect in appropriate and sufficient doses [68]. Structural heterogeneity of chondroitin sulphate, another supplement commonly taken alongside glucosamine, means that it is difficult to see consistent effects of this supplement, and the supplements available on the market are unlikely to be pure due to contamination with other glycosaminoglycans during the manufacturing process [71]. There is some evidence that glucosamine and chondroitin sulphate together provide superior effects on the inhibition of nitric oxide and prostaglandin synthesis and on protection of cartilage structure, than when applied alone [72,73].…”

A color‐code for glycosaminoglycans identification by means of polyacrylamide gel electrophoresis stained with the cationic carbocyanine dye Stains‐all

“…Once it had been determined that Stains‐all stains each GAG with distinct colors, we investigated whether this dye is useful in identifying particular GAGs present in mixtures with basis on their colors only. To avoid the usual contaminations found in raw extracts of sulfated polysaccharides such as DNA and proteins, we opted to prepare mixtures using standard GAGs as they are found in some common biomedical or pharmacological cases: hyaluronic acid and chondroitin 6‐sulfate as found in mammal cartilages ; chondroitin 6‐sulfate and keratan sulfate as found in pharmaceutical preparations of chondroitin sulfate from shark cartilages and dermatan sulfate and heparan sulfate (substituted here by heparin) as found in the urine of mucopolysaccharidosis‐I patients . In the first mixture both hyaluronic acid and chondroitin 6‐sulfate were easily distinguished by their bright‐blue and reddish‐brown colors, respectively, and also by their distinct electrophoretic mobility, that is because the high molecular weight hyaluronic acid ( M r >1.0 × 10 6 ) stays concentrated in the origin while the chondroitin 6‐sulfate ( M r ∼60 000) migrates as a polydisperse blot along the upper portion of the gel (Fig.…”

Detection of a Non-animal Source of Glycosaminoglycans from Edible Mushrooms in Northern Thailand

“…Taken together, our UV-based spectroscopy confirmed the presence of GAGs, but could not distinguish their types. Further study of the GAGs found here using magnetic resonance spectroscopy (NMR) or disaccharide analyses should be performed (Santos et al, 2017).…”